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Diimide-based semiconductor materials and methods of preparing and using the same

a technology of semiconductor materials and diimide, which is applied in the manufacture of final products, naphthalimide/phthalimide dyes, anthracene dyes, etc., can solve the problems of poor air stability and limit the type of manufacturing process (e.g., printing deposition) that can be used with n-type semiconducting compounds, and achieves the effect of useful electrical properties

Active Publication Date: 2008-08-07
FLEXTERRA INC
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0003]In the case of organic semiconductors designed for n-type (where electrons are the majority charge carriers) transistor applications, additional requirements need to be taken into consideration. These additional requirements include material compatibility in terms of LUMO (lowest unoccupied molecular orbital—equivalent to conduction band for inorganic semiconductors) energy, proper energy match with the source / drain electrodes, as well as optimized film morphology and microstructure to maximize conductivity in the transistor ON state.

Problems solved by technology

Among the limited number of promising n-type semiconductors, most of them suffer from serious drawbacks including poor stability in air and poor solubility in common organic solvents, which limit the type of manufacturing processes (e.g., printing deposition) that can be used with these n-type semiconducting compounds.

Method used

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  • Diimide-based semiconductor materials and methods of preparing and using the same
  • Diimide-based semiconductor materials and methods of preparing and using the same
  • Diimide-based semiconductor materials and methods of preparing and using the same

Examples

Experimental program
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Effect test

example 1

Preparation of N,N′-bis[(3S)-3,7-dimethyl-6-octenyl]-1,7-dicyanoperylene-3,4:9,10-bis(dicarboxiamide) (PDICitr-CN2)

Part A: Preparation of N,N′-bis[(3S)-3,7-dimethyl-6-octenyl]-1,7-dibromoperylene-3,4:9,10-bis(dicarboxiamide) (PDICitr-Br2

[0112]Citronellylamine (5.00 g, 31.8 mmol) was added to a suspension of 1,7-dibromoperylene-3,4:9,10-dianhydride (PDABr2) (4.37 g, 7.95 mmol) in propionic acid (50 mL). The reaction mixture was heated under reflux for 12 hours. After cooling to room temperature, the resulting solid was collected by filtration, washed with propionic acid and several times with methanol (MeOH), and finally dried overnight. The crude product (4.71 g) was purified by chromatography on silica gel (dichloromethane, CH2Cl2) to give N,N′-bis[(3S)-3,7-dimethyl-6-octenyl]-1,7-dibromoperylene-3,4:9,10-bis(dicarboxiamide) as a red solid (0.70 g, 0.85 mmol, 10.7% yield).

[0113]M.p.=270-272° C. (DMF); 1H NMR (CHCl3, 400 MHz): δ 9.50 (d, 2H, J=7.5 Hz), 8.94 (s, 2H), 8.72 (d, 2H, J=...

example 2

Preparation of N,N′-bis(4-n-hexylphenyl)-1,7-dicyanoperylene-3,4:9,10-bis(dicarboxiamide) (PDIPh6-CN2)

Part A: Preparation of N,N′-bis(4-n-hexylphenyl)-1,7-dibromoperylene-3,4:9,10-bis(dicarboxiamide) (PDIPh6-Br2)

[0116]4-n-Hexylaniline (3.39 g, 19.12 mmol) was added to a suspension of 1,7-dibromoperylene-3,4:9,10-dianhydride (4.00 g, 4.78 mmol) in propionic acid (40 mL). The reaction mixture was heated under reflux for 12 hours. After cooling to room temperature, the resulting solid was collected by filtration, washed with propionic acid and several times with MeOH, and finally dried overnight. The crude product (4.38 g) was purified by chromatography on silica gel (chloroform:acetone—50:50) to give N,N′-bis(4-n-hexylphenyl)-1,7-dibromoperylene-3,4:9,10-bis(dicarboxiamide) as a red solid (1.49 g, 1.72 mmol, 36.0% yield).

[0117]M.p. >250° C. (DMF); 1H NMR (CHCl3, 400 MHz): δ 9.54 (d, 2H, J=8.0 Hz), 8.96 (s, 2H), 8.76 (d, 2H, J=8.0 Hz), 7.40 (d, 4H, J=8.0 Hz), 7.24 (d, 4H, J=8.0 Hz), 2....

example 3

Preparation of N,N′-bis(4-n-dodecylphenyl)-1,7-dicyanoperylene-3,4:9,10-bis(dicarboxiamide) (PDIPh12-CN2)

Part A: Preparation of N,N′-bis(4-n-dodecylphenyl)-1,7-dibromoperylene-3,4:9,10-bis(dicarboxiamide) (PDIPh12-Br2)

[0120]4-Dodecylaniline (5.00 g, 19.12 mmol) was added to a suspension of 1,7-dibromoperylene-3,4:9,10-dianhydride (2.63 g, 4.78 mmol) in propionic acid (52.5 mL). The reaction mixture was heated under reflux for 12 hours. After cooling to room temperature, the resulting solid was collected by filtration, washed with propionic acid and several times with MeOH, and finally dried overnight. The crude product (3.25 g) was extracted using a Soxhlet extractor with chloroform (CHCl3, 500 mL) over 2 days and the resulting solid was purified by chromatography on silica gel (CH2Cl2) to afford N,N′-bis(4-n-dodecylphenyl)-1,7-dibromoperylene-3,4:9,10-bis(dicarboxiamide) as a red solid (1.20 g, 1.11 mmol, 24.2% yield).

[0121]M.p. >300° C. (DMF); 1H NMR (CHCl3, 500 MHz): δ 9.58 (d, 2...

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Abstract

Diimide-based semiconductor materials are provided with processes for preparing the same. Composites and electronic devices including the diimide-based semiconductor materials also are provided.

Description

CROSS REFERENCE TO RELATED APPLICATION[0001]This application claims priority to and the benefit of U.S. Provisional Patent Application Ser. No. 60 / 859,761, filed on Nov. 17, 2006.INTRODUCTION[0002]The electronic structure of most organic semiconductors consists of delocalized π orbitals within a molecular / polymeric σ framework that mainly constitutes sp2 hybridized carbon atoms and to some extent, heteroatoms such as sulfur, selenium, nitrogen, and oxygen. The primary mechanism for charge transport in organic solids is based on efficient molecular / polymer chain stacking which results in π-π orbital interaction, allowing the charge carriers injected at the electrical contacts to migrate from molecule to molecule (chain to chain).[0003]In the case of organic semiconductors designed for n-type (where electrons are the majority charge carriers) transistor applications, additional requirements need to be taken into consideration. These additional requirements include material compatibili...

Claims

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Application Information

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IPC IPC(8): H01L51/30C07D471/02B05D1/02B05D1/18C23C16/44H01B1/00
CPCC07D471/06C07D487/06H01L51/0053Y02E10/549C09B5/62C09B57/08H01L51/0545Y02P70/50H10K85/621H10K10/466
Inventor FACCHETTI, ANTONIOMARKS, TOBIN J.YAN, HE
Owner FLEXTERRA INC
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